tert-butanesulfinamide and allyl-bromide

The combination of an aldehyde, an allylic bromide, and tert-butanesulfinamide in the presence of indium metal and titanium tetraethoxide allows straightforward access to homoallylamine derivatives in high yields and stereoselectivities. Moreover, the synthetic utility of the enantioenriched homoallylamine derived from n-decanal was illustrated in a concise synthesis of (+)-isosolenopsin. In this context, similar homoallylamines has been recently used by other groups in the synthesis of naturally occurring alkaloids.

Topics: Aldehydes; Alkylation; Allyl Compounds; Allylamine; Butanes; Crystallography, X-Ray; Models, Molecular; Molecular Structure; Stereoisomerism; Sulfonamides